I've switched from PC speakers to "real" speakers and I'm quite happy I did.
It's funny hearing about the "big" logitech and Klipsch subs now
http://pics.bbzzdd.com/users/YOyoYOhowsDAjello/SVS_vs_Log_z-560.JPG
Definately a lot more options if you don't limit yourself to computer speakers.
If your long term plan for this system is an evolution into a hometheater system, getting a surround sound receiver an 2.0 / 2.1 speakers going is going to offer you the best upgrade path.
This isn't the answer for everyone though. If you just want 5.1 now, you could get one of the nicer computer speaker sets or an entry level HTIB.
If your primary concern is music though, it seems to make sense to try to get the best speakers you can in your budget.
For soundcard, you can go really cheap. In fact, if the computer you're going to use has integrated digital out, you can just use that. This will work find for music and movies. Not to good for gaming though. If gaming is a concern to you, then you should look into the usual audigy / X-Fi suspects and get a receiver with a 5.1 (or higher) multichannel input.... OR.... you could get a card that does Dolby Digital Live / DTS Live and then get whatever modern receiver you want with digital inputs.
If you want to get a soundcard but don't care about games, then the Chaintech AV-710 is a nice card for digital out. About $25-$30 over here.
What should you look for? Generally something cheap
It's going to make a much bigger difference what speakers you choose vs the receiver. Get a cheap Pioneer / Onkyo / etc.
You can get a decent receiver for around $200 US over here. I'm not sure exactly where you should look to get a good deal up there.
For connection options, your options are probably going to be pretty similar. For video opitons, if your display has several inputs, it's not really necessary to go through the receiver, so audio is going to be the main thing. Pretty much any modern receiver is going to have several digital inputs (optical or coaxial), so you should be set for most sources. The 5.1 multichannel input might cost you, as entry level receivers tend not to have that input.
Most sources you're going to be using with your HDTV are going to be digital. Pretty much anything "surround" is going to be a digital source.
For features, there aren't going to be a whole lot of differences at this pricerange either. I don't think there's a "must have" feature you should be looking for. There's auto-setup, auto-equalization, 2nd zone, HDMI inputs, etc., but you're not going to have a whole lot of options really... so don't worry about it.
If you just want to look around to get your feet wet, check out
http://www.avsforum.com/avs-vb/
More info and opinions over there than you'll ever be able to read.
If you go receiver/speakers route, the most important decision is probably going to be your speakers. For any budget you name (even into hundreds of thousands of dollars), there are speaker options for you. Assuming you spend around $200 on a budget receiver, that would leave you ~$300 for speakers or speakers/sub. Depending on what you want to do, you could get a decent set of bookshelf speakers for that much, or get some entry level speakers and a sub. I thin you're going to have to figure out what your long term plans are before deciding what you want to do.
One common way to go would be to buy just a pair of bookshelf speakers and then add to it as you go. As in, get the best speakers you can afford for now and worry about adding things like a sub later. To get a final surround set going, you could add a sub, then a center channel, and then get new front speakers and move your originals to surround duty.
This can eat into your wallet pretty quickly. If you don't think you want to add to the system as you go, you might want to just get a HTIB system. You'll have 5.1 from the get go but you'll still be able to make changes later if you want to. Onkyo sets are nice since their receivers are a good starting point that you can keep in your system after you start upgrading. You might be the kind of guy that's totally happy with the original purchase too.
Ok, now I'm just rambling... sorry
EDIT: hey, might as well use it even though it's an unorganized, incomplete mess...
http://forums.anandtech.com/messageview...atid=30&threadid=1810562&enterthread=y
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